Hydrocarbons and their derivatives are involved in practically all aspects of our every day life. Many of these compounds, however, also represent significant health hazards, not yet investigated or understood to a full extent. Study of the potential bioalkylating ability of major types of hydrocarbons (alkanes, cycloalkanes, alkenes, alkynes and arenes) and some of their industrially significant derivatives will be carried out. The potential alkylating agents which can be formed including carbocationic, as well oxonium, halonium and related onium type compounds will be studied by various methods previously developed in our laboratory work. The latter studies will emphasize activation of various hydrocarbons forming via one, and two-electron transfer processes radications, carbocations, and carbodications, respectively, Carbon-13 nmr studies will further probe the relationship between charge distribution patterns and alkylating ability. Selectivity of alkylating and acylation systems against different biologically significant substrates will be also studied with emphasis on the question of electronic and steric factors. Particular emphasis will be given to the activation of polycyclic aromatics to form potential alkylating agents via oxyfunctionalization pathways, involving intermediacy of arene oxides and their opening reactions. Functionalized hydrocarbons to be studied will include halides, amines (including nitrosamines), various carboxylic and sulfonic acid derivatives (including such controversial derivatives as saccharin) and other industrially significant derivatives, which can form potential alkylating or acylating agents. Identification of such active alkylating (acylating) agents, their formation mechanism, and possible relationship to biological conditions will be investigated. Novel aspects of formation of biomonomers from simple chemical building blocks will also be studied, such as CH4, HCN, CO, etc., using acidic clay, and related catalysts. The understanding of the formation and alkylative behavior of simple biomonomers under conditions relating to prebiological environments should further our knowledge on hydrocarbon transformation.